I am organizing a group day trip from Orvieto and I have quote for a tour bus with driver who will basically take us where directed picking us up in Orvieto at 9 am and returning at 5. We would like to see Montepulciano, Pienza and visit a vineyard for a wine tasting. The bus company will arrange the wine tasting and we will pay the driver the day of. I'm trying to decide on a nice scenic restaurant for lunch and saw Terrazza Val d'Orcia in Pienza and also La Guardiola in Monticchiello. Does anyone have any pros or cons for either?
How much time should we allow for Montepulciano and Pienza? I notice that Thursday is market day in Montepulciano which is the day we would be visiting. Should we plan to visit there in the morning during the market or afternoon to avoid it?

Any suggestions or recommendations would be greatly appreciated.

topping

Even with a driver, I think this is a bit much for an 8-hour group excursion. You don't mention how large the group is, but our experience is that moving groups of any size beyond 4 takes longer no matter how well-intentioned everyone is. I think it's safe to say, the larger the group the more time everything takes.

Beyond that issue, the drive alone could eat up 3 of your 8 hours, and traveling on the more interesting secondary roads rather than the autostrada could easily add another 30-45 minutes overall. Keep in mind that the bus won't be allowed to drop/load your group in the center of any town, so you need to factor in some time to walk from/to where the bus can park.

You could have a wine experience at a tasting room in either Montepulciano or Pienza rather than making yet another drive and stop at a winery. I can't comment on either restaurant you're considering, but I suggest you read reviews very carefully to determine whether a group of your size can be accommodated without delays in service. If your visit is in summer, I'd make sure any outdoor seating has lots and lots of shade. I don't know anything about your group, but would it be possible/appropriate for everyone to get lunch on their own? On the very few occasions we've been in a group, we've chosen to grab a quick lunch and continue exploring rather than spend time sitting in a restaurant.

Depending on the groups' interests and/or the experience you're trying to create for them, you might consider visiting only one of the two towns you mention, having lunch and the wine experience there, and then making a short stop at the Abbey of Sant'Antimo on your way back to Orvieto.

Thanks very much Jean. You've made some great points which we'll need to consider to fine-tune the day. We have about 13 in our group. And you're right it is hard to herd a group that size We can add more time if we like and I like your idea of everyone having lunch on their own. I'll canvas the group to ask their preference.

We had a nice wine tasting experience and lunch at Gattevecchi in Montepulciano. The patio had a nice view, the wine was amazing and the food was fabulous. It is on the outer edge of town so access would be easier with your bus.
https://www.cantinagattavecchi.com/en/

Thanks Werth. I'll check it out.